OA12969A - Combination for the treatment of ADHD. - Google Patents

Combination for the treatment of ADHD. Download PDF

Info

Publication number: OA12969A
Authority: OA; OAPI
Prior art keywords: azabicyclo; substituted; carboxamide; alkyl; oct
Prior art date: 2002-12-11

Application number

OA1200500174A

Other languages

English (en)

Inventor

Donn Gregory Wishka

Vincent Edward Groppi Jr

Eric Jon Jacobsen

Jason Kenneth Myers

David Walter Piotrowski

Bruce Nelsen Rogers

Daniel Patrick Walker

Original Assignee

Pharmacia & Upjohn Co Llc

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

2002-12-11

Filing date

2003-11-28

Publication date

2006-10-13

2003-11-28 Application filed by Pharmacia & Upjohn Co Llc filed Critical Pharmacia & Upjohn Co Llc

2006-10-13 Publication of OA12969A publication Critical patent/OA12969A/en

Links

208000006096 Attention Deficit Disorder with Hyperactivity Diseases 0.000 title claims abstract description 6
208000036864 Attention deficit/hyperactivity disease Diseases 0.000 title claims abstract description 5
239000000203 mixture Substances 0.000 claims abstract description 275
239000000556 agonist Substances 0.000 claims abstract description 33
239000003368 psychostimulant agent Substances 0.000 claims abstract description 25
102000015296 acetylcholine-gated cation-selective channel activity proteins Human genes 0.000 claims abstract 5
108040006409 acetylcholine-gated cation-selective channel activity proteins Proteins 0.000 claims abstract 5
125000000217 alkyl group Chemical group 0.000 claims description 152
125000000592 heterocycloalkyl group Chemical group 0.000 claims description 142
125000001188 haloalkyl group Chemical group 0.000 claims description 117
229910052731 fluorine Inorganic materials 0.000 claims description 113
125000001424 substituent group Chemical group 0.000 claims description 111
125000000753 cycloalkyl group Chemical group 0.000 claims description 109
229910052794 bromium Inorganic materials 0.000 claims description 105
229910052801 chlorine Inorganic materials 0.000 claims description 104
125000000547 substituted alkyl group Chemical group 0.000 claims description 98
150000001875 compounds Chemical class 0.000 claims description 94
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 94
-1 -ORn Chemical group 0.000 claims description 93
125000005347 halocycloalkyl group Chemical group 0.000 claims description 74
229910052740 iodine Inorganic materials 0.000 claims description 72
229910052799 carbon Inorganic materials 0.000 claims description 58
229910052757 nitrogen Inorganic materials 0.000 claims description 58
125000004093 cyano group Chemical group *C#N 0.000 claims description 55
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 50
125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 49
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 46
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 38
125000000304 alkynyl group Chemical group 0.000 claims description 36
229910052739 hydrogen Inorganic materials 0.000 claims description 36
125000003118 aryl group Chemical group 0.000 claims description 34
229910052760 oxygen Inorganic materials 0.000 claims description 33
125000003342 alkenyl group Chemical group 0.000 claims description 32
125000005017 substituted alkenyl group Chemical group 0.000 claims description 28
125000000262 haloalkenyl group Chemical group 0.000 claims description 26
125000000232 haloalkynyl group Chemical group 0.000 claims description 26
125000004426 substituted alkynyl group Chemical group 0.000 claims description 26
125000001624 naphthyl group Chemical group 0.000 claims description 24
229910052717 sulfur Inorganic materials 0.000 claims description 24
125000004432 carbon atom Chemical group C* 0.000 claims description 19
229940126403 monoamine reuptake inhibitor Drugs 0.000 claims description 16
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 14
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 12
DFPAKSUCGFBDDF-UHFFFAOYSA-N Nicotinamide Chemical compound NC(=O)C1=CC=CN=C1 DFPAKSUCGFBDDF-UHFFFAOYSA-N 0.000 claims description 10
VHGCDTVCOLNTBX-QGZVFWFLSA-N atomoxetine Chemical compound O([C@H](CCNC)C=1C=CC=CC=1)C1=CC=CC=C1C VHGCDTVCOLNTBX-QGZVFWFLSA-N 0.000 claims description 9
UZVGSSNIUNSOFA-UHFFFAOYSA-N dibenzofuran-1-carboxylic acid Chemical compound O1C2=CC=CC=C2C2=C1C=CC=C2C(=O)O UZVGSSNIUNSOFA-UHFFFAOYSA-N 0.000 claims description 8
239000003814 drug Substances 0.000 claims description 8
125000006239 protecting group Chemical group 0.000 claims description 8
235000005152 nicotinamide Nutrition 0.000 claims description 7
239000011570 nicotinamide Substances 0.000 claims description 7
YFGHCGITMMYXAQ-UHFFFAOYSA-N 2-[(diphenylmethyl)sulfinyl]acetamide Chemical compound C=1C=CC=CC=1C(S(=O)CC(=O)N)C1=CC=CC=C1 YFGHCGITMMYXAQ-UHFFFAOYSA-N 0.000 claims description 6
HCYAFALTSJYZDH-UHFFFAOYSA-N Desimpramine Chemical group C1CC2=CC=CC=C2N(CCCNC)C2=CC=CC=C21 HCYAFALTSJYZDH-UHFFFAOYSA-N 0.000 claims description 6
229960002430 atomoxetine Drugs 0.000 claims description 6
SNPPWIUOZRMYNY-UHFFFAOYSA-N bupropion Chemical compound CC(C)(C)NC(C)C(=O)C1=CC=CC(Cl)=C1 SNPPWIUOZRMYNY-UHFFFAOYSA-N 0.000 claims description 6
101001043818 Mus musculus Interleukin-31 receptor subunit alpha Proteins 0.000 claims description 5
125000004429 atom Chemical group 0.000 claims description 5
IQQNMLSLUVURHZ-UHFFFAOYSA-N furo[2,3-c]pyridine-5-carboxamide Chemical compound C1=NC(C(=O)N)=CC2=C1OC=C2 IQQNMLSLUVURHZ-UHFFFAOYSA-N 0.000 claims description 5
CZXIPBIBWCODNX-UHFFFAOYSA-N thieno[2,3-c]pyridine-5-carboxamide Chemical compound C1=NC(C(=O)N)=CC2=C1SC=C2 CZXIPBIBWCODNX-UHFFFAOYSA-N 0.000 claims description 5
TUPZWIXDHKKDRH-UHFFFAOYSA-N thieno[3,2-c]pyridine-6-carboxamide Chemical compound C1=NC(C(=O)N)=CC2=C1C=CS2 TUPZWIXDHKKDRH-UHFFFAOYSA-N 0.000 claims description 5
241000124008 Mammalia Species 0.000 claims description 4
125000002619 bicyclic group Chemical group 0.000 claims description 4
125000005842 heteroatom Chemical group 0.000 claims description 4
125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
NRNCYVBFPDDJNE-UHFFFAOYSA-N pemoline Chemical compound O1C(N)=NC(=O)C1C1=CC=CC=C1 NRNCYVBFPDDJNE-UHFFFAOYSA-N 0.000 claims description 4
RTHCYVBBDHJXIQ-MRXNPFEDSA-N (R)-fluoxetine Chemical compound O([C@H](CCNC)C=1C=CC=CC=1)C1=CC=C(C(F)(F)F)C=C1 RTHCYVBBDHJXIQ-MRXNPFEDSA-N 0.000 claims description 3
PYHRZPFZZDCOPH-QXGOIDDHSA-N (S)-amphetamine sulfate Chemical compound [H+].[H+].[O-]S([O-])(=O)=O.C[C@H](N)CC1=CC=CC=C1.C[C@H](N)CC1=CC=CC=C1 PYHRZPFZZDCOPH-QXGOIDDHSA-N 0.000 claims description 3
LPCQBTAOTIZGAE-UHFFFAOYSA-N 2h-pyrimidine-1-carboxamide Chemical compound NC(=O)N1CN=CC=C1 LPCQBTAOTIZGAE-UHFFFAOYSA-N 0.000 claims description 3
RTHCYVBBDHJXIQ-UHFFFAOYSA-N N-methyl-3-phenyl-3-[4-(trifluoromethyl)phenoxy]propan-1-amine Chemical compound C=1C=CC=CC=1C(CCNC)OC1=CC=C(C(F)(F)F)C=C1 RTHCYVBBDHJXIQ-UHFFFAOYSA-N 0.000 claims description 3
229940047812 adderall Drugs 0.000 claims description 3
229960001058 bupropion Drugs 0.000 claims description 3
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
150000003857 carboxamides Chemical class 0.000 claims description 3
229940099242 dexedrine Drugs 0.000 claims description 3
229960002464 fluoxetine Drugs 0.000 claims description 3
239000012458 free base Substances 0.000 claims description 3
125000001072 heteroaryl group Chemical group 0.000 claims description 3
125000000623 heterocyclic group Chemical group 0.000 claims description 3
JUMYIBMBTDDLNG-UHFFFAOYSA-N methylphenidate hydrochloride Chemical group [Cl-].C=1C=CC=CC=1C(C(=O)OC)C1CCCC[NH2+]1 JUMYIBMBTDDLNG-UHFFFAOYSA-N 0.000 claims description 3
229960001165 modafinil Drugs 0.000 claims description 3
229940087480 norpramin Drugs 0.000 claims description 3
229960000761 pemoline Drugs 0.000 claims description 3
229940117394 provigil Drugs 0.000 claims description 3
229940035613 prozac Drugs 0.000 claims description 3
JHAAOICPGQBYGL-UHFFFAOYSA-N pyrrolo[1,2-c]pyrimidine-3-carboxamide Chemical compound C1=NC(=CC=2N1C=CC=2)C(=O)N JHAAOICPGQBYGL-UHFFFAOYSA-N 0.000 claims description 3
CBQGYUDMJHNJBX-RTBURBONSA-N reboxetine Chemical compound CCOC1=CC=CC=C1O[C@H](C=1C=CC=CC=1)[C@@H]1OCCNC1 CBQGYUDMJHNJBX-RTBURBONSA-N 0.000 claims description 3
229960003770 reboxetine Drugs 0.000 claims description 3
229940012488 strattera Drugs 0.000 claims description 3
229940009065 wellbutrin Drugs 0.000 claims description 3
125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 claims description 2
IPKZCLGGYKRDES-ZDUSSCGKSA-N Pha-543613 Chemical compound N([C@@H]1C2CCN(CC2)C1)C(=O)C(N=C1)=CC2=C1OC=C2 IPKZCLGGYKRDES-ZDUSSCGKSA-N 0.000 claims description 2
229960003914 desipramine Drugs 0.000 claims description 2
TVFIYRKPCACCNL-UHFFFAOYSA-N furan-2-carboxamide Chemical compound NC(=O)C1=CC=CO1 TVFIYRKPCACCNL-UHFFFAOYSA-N 0.000 claims description 2
UTXFCHDGQZNPQX-VHDGCEQUSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-ethynyl-1-benzofuran-5-carboxamide Chemical compound C1=C2OC=C(C#C)C2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 UTXFCHDGQZNPQX-VHDGCEQUSA-N 0.000 claims description 2
HGKVHUCIRKTUEL-HZSPNIEDSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-6-chloroisoquinoline-3-carboxamide Chemical compound ClC1=CC=C2C=NC(C(=O)N[C@H]3[C@]4([H])CC[C@@](N4)(C3)[H])=CC2=C1 HGKVHUCIRKTUEL-HZSPNIEDSA-N 0.000 claims description 2
ZKKGMKJDVSZXBI-UGSOOPFHSA-N n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]naphthalene-2-carboxamide Chemical compound C1CC2CCN1[C@@H](C)[C@@H]2NC(=O)C1=CC=C(C=CC=C2)C2=C1 ZKKGMKJDVSZXBI-UGSOOPFHSA-N 0.000 claims description 2
LGWFAAILRNJWJB-AWEZNQCLSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-1-benzofuran-6-carboxamide Chemical compound C1=C2C=COC2=CC(C(N[C@@H]2C3CCN(CC3)C2)=O)=C1 LGWFAAILRNJWJB-AWEZNQCLSA-N 0.000 claims description 2
DPSFSXMSAJMDPZ-HNNXBMFYSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-1-methylindole-6-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=CC=C2C=CN(C)C2=C1 DPSFSXMSAJMDPZ-HNNXBMFYSA-N 0.000 claims description 2
CPYLAMFWQOHAQI-HNNXBMFYSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-cyano-1-benzofuran-5-carboxamide Chemical compound C1=C2OC=C(C#N)C2=CC(C(N[C@@H]2C3CCN(CC3)C2)=O)=C1 CPYLAMFWQOHAQI-HNNXBMFYSA-N 0.000 claims description 2
MLQQWDWROFCCOB-KRWDZBQOSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-6-methylisoquinoline-3-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=CC2=CC(C)=CC=C2C=N1 MLQQWDWROFCCOB-KRWDZBQOSA-N 0.000 claims description 2
BNUIMNKNBBSGKZ-KRWDZBQOSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-7-hydroxynaphthalene-2-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=CC2=CC(O)=CC=C2C=C1 BNUIMNKNBBSGKZ-KRWDZBQOSA-N 0.000 claims description 2
JHRRADCVOUYBLD-KRWDZBQOSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]dibenzothiophene-2-carboxamide Chemical compound C1=CC=C2C3=CC(C(N[C@@H]4C5CCN(CC5)C4)=O)=CC=C3SC2=C1 JHRRADCVOUYBLD-KRWDZBQOSA-N 0.000 claims description 2
SJUAXKQQDBQMMM-HNNXBMFYSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]indolizine-6-carboxamide Chemical compound C1=CC2=CC=CN2C=C1C(=O)N[C@@H]1C(CC2)CCN2C1 SJUAXKQQDBQMMM-HNNXBMFYSA-N 0.000 claims description 2
CAAYBIHYHYDTMB-INIZCTEOSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]isoquinoline-3-carboxamide Chemical compound C1=CC=C2C=NC(C(N[C@@H]3C4CCN(CC4)C3)=O)=CC2=C1 CAAYBIHYHYDTMB-INIZCTEOSA-N 0.000 claims description 2
FSWJILNACZEMQN-AWEZNQCLSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]thieno[3,4-c]pyridine-6-carboxamide Chemical compound C=1C2=CSC=C2C=NC=1C(=O)N[C@@H]1C(CC2)CCN2C1 FSWJILNACZEMQN-AWEZNQCLSA-N 0.000 claims description 2
125000002943 quinolinyl group Chemical group N1=C(C=CC2=CC=CC=C12)* 0.000 claims description 2
230000001225 therapeutic effect Effects 0.000 claims description 2
KWTSXDURSIMDCE-QMMMGPOBSA-N (S)-amphetamine Chemical compound C[C@H](N)CC1=CC=CC=C1 KWTSXDURSIMDCE-QMMMGPOBSA-N 0.000 claims 2
PHVGLTMQBUFIQQ-UHFFFAOYSA-N Nortryptiline Chemical compound C1CC2=CC=CC=C2C(=CCCNC)C2=CC=CC=C21 PHVGLTMQBUFIQQ-UHFFFAOYSA-N 0.000 claims 2
229960000632 dexamfetamine Drugs 0.000 claims 2
229960001158 nortriptyline Drugs 0.000 claims 2
VPABXAQVSOGZEM-LBPRGKRZSA-N 2-amino-n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-1,3-benzothiazole-6-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=CC=C2N=C(N)SC2=C1 VPABXAQVSOGZEM-LBPRGKRZSA-N 0.000 claims 1
LYSMTLRFEXVZHX-VFZGTOFNSA-N 3-bromo-n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]furo[2,3-c]pyridine-5-carboxamide Chemical compound C1CC2CCN1[C@@H](C)[C@@H]2NC(=O)C(N=C1)=CC2=C1OC=C2Br LYSMTLRFEXVZHX-VFZGTOFNSA-N 0.000 claims 1
VHGPPUNISVTOTA-ZBEGNZNMSA-N 3-methyl-n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]furo[2,3-c]pyridine-5-carboxamide Chemical compound C1CC2CCN1[C@@H](C)[C@@H]2NC(=O)C(N=C1)=CC2=C1OC=C2C VHGPPUNISVTOTA-ZBEGNZNMSA-N 0.000 claims 1
NHANKJDOPVCXFZ-UHFFFAOYSA-N [1]benzothiolo[2,3-c]pyridine-3-carboxamide Chemical compound S1C2=CC=CC=C2C2=C1C=NC(C(=O)N)=C2 NHANKJDOPVCXFZ-UHFFFAOYSA-N 0.000 claims 1
HESCDCQCRMYSQH-PPKCKEKNSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-bromothieno[2,3-c]pyridine-5-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1SC=C2Br HESCDCQCRMYSQH-PPKCKEKNSA-N 0.000 claims 1
ZHATVBLTFXQKKQ-UHOFOFEASA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-3-propan-2-yl-1-benzofuran-5-carboxamide Chemical compound C1=C2OC=C(C(C)C)C2=CC(C(=O)N[C@H]2[C@]3([H])CC[C@@](N3)(C2)[H])=C1 ZHATVBLTFXQKKQ-UHOFOFEASA-N 0.000 claims 1
DSDXBWWMQGRMTF-HRDYMLBCSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]-[1,3]dioxolo[4,5-c]pyridine-6-carboxamide Chemical compound N([C@H]1[C@]2([H])CC[C@@](N2)(C1)[H])C(=O)C(N=C1)=CC2=C1OCO2 DSDXBWWMQGRMTF-HRDYMLBCSA-N 0.000 claims 1
UROOPEBYODQRCX-UHOFOFEASA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]dibenzothiophene-2-carboxamide Chemical compound C1=CC=C2C3=CC(C(=O)N[C@H]4[C@]5([H])CC[C@@](N5)(C4)[H])=CC=C3SC2=C1 UROOPEBYODQRCX-UHOFOFEASA-N 0.000 claims 1
MPCJMRQULBKSGV-ADEWGFFLSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]pyrrolo[1,2-a]pyrazine-3-carboxamide Chemical compound C=1N2C=CC=C2C=NC=1C(=O)N[C@H](C1)[C@]2([H])CC[C@@]1([H])N2 MPCJMRQULBKSGV-ADEWGFFLSA-N 0.000 claims 1
LQWOQWNXBDDFAU-ADEWGFFLSA-N n-[(1r,3r,4s)-7-azabicyclo[2.2.1]heptan-3-yl]pyrrolo[1,2-c]pyrimidine-3-carboxamide Chemical compound C=1C2=CC=CN2C=NC=1C(=O)N[C@H](C1)[C@]2([H])CC[C@@]1([H])N2 LQWOQWNXBDDFAU-ADEWGFFLSA-N 0.000 claims 1
SGSVFNIEMVSPSP-LRDDRELGSA-N n-[(2s,3r)-2-methyl-1-azabicyclo[2.2.2]octan-3-yl]indolizine-6-carboxamide Chemical compound C1CC2CCN1[C@@H](C)[C@@H]2NC(=O)C1=CN2C=CC=C2C=C1 SGSVFNIEMVSPSP-LRDDRELGSA-N 0.000 claims 1
ZLYNXTYFPVYJKB-ZDUSSCGKSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-1,3-benzothiazole-6-carboxamide Chemical compound C1=C2N=CSC2=CC(C(N[C@@H]2C3CCN(CC3)C2)=O)=C1 ZLYNXTYFPVYJKB-ZDUSSCGKSA-N 0.000 claims 1
CXDMUUBLDHSHNL-AWEZNQCLSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-1-benzofuran-5-carboxamide Chemical compound C1=C2OC=CC2=CC(C(N[C@@H]2C3CCN(CC3)C2)=O)=C1 CXDMUUBLDHSHNL-AWEZNQCLSA-N 0.000 claims 1
YGTNJCNUBHRGNM-AWEZNQCLSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-2,3-dihydro-1-benzofuran-5-carboxamide Chemical compound C1=C2OCCC2=CC(C(N[C@@H]2C3CCN(CC3)C2)=O)=C1 YGTNJCNUBHRGNM-AWEZNQCLSA-N 0.000 claims 1
LIPFPTTWJOEZMN-HNNXBMFYSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-2h-chromene-6-carboxamide Chemical compound O1CC=CC2=CC(C(N[C@@H]3C4CCN(CC4)C3)=O)=CC=C21 LIPFPTTWJOEZMN-HNNXBMFYSA-N 0.000 claims 1
YCSBGDZYEYEBHT-ZDUSSCGKSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-chlorofuro[2,3-c]pyridine-5-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NC=C2OC=C(Cl)C2=C1 YCSBGDZYEYEBHT-ZDUSSCGKSA-N 0.000 claims 1
JJEYDHWWUYPKDW-KRWDZBQOSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-prop-1-ynyl-1-benzofuran-5-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=CC=C2OC=C(C#CC)C2=C1 JJEYDHWWUYPKDW-KRWDZBQOSA-N 0.000 claims 1
XGRQNDGMEYPKIB-INIZCTEOSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-prop-1-ynylfuro[2,3-c]pyridine-5-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=NC=C2OC=C(C#CC)C2=C1 XGRQNDGMEYPKIB-INIZCTEOSA-N 0.000 claims 1
HYRFDAUWCLPERX-KRWDZBQOSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-3-propan-2-yl-1-benzofuran-5-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=CC=C2OC=C(C(C)C)C2=C1 HYRFDAUWCLPERX-KRWDZBQOSA-N 0.000 claims 1
VLQHCUFLQYLUIY-KRWDZBQOSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]-8-methoxynaphthalene-2-carboxamide Chemical compound C1N(CC2)CCC2[C@H]1NC(=O)C1=CC=C2C=CC=C(OC)C2=C1 VLQHCUFLQYLUIY-KRWDZBQOSA-N 0.000 claims 1
PPNRSNVMBVPXCM-KRWDZBQOSA-N n-[(3r)-1-azabicyclo[2.2.2]octan-3-yl]dibenzofuran-2-carboxamide Chemical compound C1=CC=C2C3=CC(C(N[C@@H]4C5CCN(CC5)C4)=O)=CC=C3OC2=C1 PPNRSNVMBVPXCM-KRWDZBQOSA-N 0.000 claims 1
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230000008034 disappearance Effects 0.000 description 2
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230000005764 inhibitory process Effects 0.000 description 2
150000007529 inorganic bases Chemical class 0.000 description 2
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LSEFCHWGJNHZNT-UHFFFAOYSA-M methyl(triphenyl)phosphanium;bromide Chemical compound [Br-].C=1C=CC=CC=1[P+](C=1C=CC=CC=1)(C)C1=CC=CC=C1 LSEFCHWGJNHZNT-UHFFFAOYSA-M 0.000 description 2
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230000004112 neuroprotection Effects 0.000 description 2
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CWMFRHBXRUITQE-UHFFFAOYSA-N trimethylsilylacetylene Chemical group C[Si](C)(C)C#C CWMFRHBXRUITQE-UHFFFAOYSA-N 0.000 description 1
YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 1
238000003828 vacuum filtration Methods 0.000 description 1
210000004515 ventral tegmental area Anatomy 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
238000010626 work up procedure Methods 0.000 description 1
235000005074 zinc chloride Nutrition 0.000 description 1
239000011592 zinc chloride Substances 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K45/00—Medicinal preparations containing active ingredients not provided for in groups A61K31/00 - A61K41/00
- A61K45/06—Mixtures of active ingredients without chemical characterisation, e.g. antiphlogistics and cardiaca
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/435—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having six-membered rings with one nitrogen as the only ring hetero atom
- A61K31/46—8-Azabicyclo [3.2.1] octane; Derivatives thereof, e.g. atropine, cocaine
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
- A61P25/00—Drugs for disorders of the nervous system

Landscapes

Health & Medical Sciences (AREA)
Chemical & Material Sciences (AREA)
Medicinal Chemistry (AREA)
Pharmacology & Pharmacy (AREA)
Life Sciences & Earth Sciences (AREA)
Animal Behavior & Ethology (AREA)
General Health & Medical Sciences (AREA)
Public Health (AREA)
Veterinary Medicine (AREA)
Epidemiology (AREA)
Emergency Medicine (AREA)
Biomedical Technology (AREA)
Organic Chemistry (AREA)
Neurology (AREA)
Neurosurgery (AREA)
Chemical Kinetics & Catalysis (AREA)
General Chemical & Material Sciences (AREA)
Nuclear Medicine, Radiotherapy & Molecular Imaging (AREA)
Bioinformatics & Cheminformatics (AREA)
Engineering & Computer Science (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Medicines That Contain Protein Lipid Enzymes And Other Medicines (AREA)
Nitrogen Condensed Heterocyclic Rings (AREA)
Mechanical Treatment Of Semiconductor (AREA)
Developing Agents For Electrophotography (AREA)
Liquid Crystal Substances (AREA)

OA1200500174A 2002-12-11 2003-11-28 Combination for the treatment of ADHD. OA12969A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US43258602P	2002-12-11	2002-12-11

Publications (1)

Publication Number	Publication Date
OA12969A true OA12969A (en)	2006-10-13

Family

ID=32507968

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
OA1200500174A OA12969A (en)	2002-12-11	2003-11-28	Combination for the treatment of ADHD.

Country Status (23)

Country	Link
US (1)	US20050107425A1 (pl)
EP (1)	EP1572300A1 (pl)
JP (1)	JP2006510663A (pl)
KR (1)	KR20050085538A (pl)
CN (1)	CN1735441A (pl)
AP (1)	AP2005003336A0 (pl)
AU (1)	AU2003283656A1 (pl)
BR (1)	BR0317229A (pl)
CA (1)	CA2509142A1 (pl)
CO (1)	CO5700801A2 (pl)
CR (1)	CR7868A (pl)
EA (1)	EA200500783A1 (pl)
EC (1)	ECSP055852A (pl)
HR (1)	HRP20050522A2 (pl)
IS (1)	IS7858A (pl)
MA (1)	MA27606A1 (pl)
MX (1)	MXPA05006336A (pl)
NO (1)	NO20053185L (pl)
OA (1)	OA12969A (pl)
PL (1)	PL377552A1 (pl)
TN (1)	TNSN05158A1 (pl)
WO (1)	WO2004052461A1 (pl)
ZA (1)	ZA200504338B (pl)

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DE10164139A1 (de)	2001-12-27	2003-07-10	Bayer Ag	2-Heteroarylcarbonsäureamide
GB0310867D0 (en)	2003-05-12	2003-06-18	Novartis Ag	Organic compounds
RU2417225C2 (ru)	2004-03-25	2011-04-27	Мемори Фармасьютиклз Корпорейшн	Индазолы, бензотиазолы, бензоизотиазолы, бензизоксазолы и их получение и применение
GB0424564D0 (en) *	2004-11-05	2004-12-08	Novartis Ag	Organic compounds
WO2008083442A1 (en) *	2007-01-10	2008-07-17	Brc Operations Pty Limited	Method for formulating combination medications for adhd
CA2681934A1 (en) *	2007-03-28	2008-10-02	High Point Pharmaceuticals, Llc	11beta-hsd1 active compounds
SA08290475B1 (ar)	2007-08-02	2013-06-22	Targacept Inc	(2s، 3r)-n-(2-((3-بيردينيل)ميثيل)-1-آزا بيسيكلو[2، 2، 2]أوكت-3-يل)بنزو فيوران-2-كربوكساميد، وصور أملاحه الجديدة وطرق استخدامه
NZ594937A (en) *	2008-02-19	2013-03-28	Adolor Corp	Beloxepin, its enantiomers, and analogs thereof for the treatment of pain
MX2011005037A (es)	2008-11-21	2011-06-16	High Point Pharmaceuticals Llc	Compuestos de adamantilo benzamida.
TW201031664A (en)	2009-01-26	2010-09-01	Targacept Inc	Preparation and therapeutic applications of (2S,3R)-N-2-((3-pyridinyl)methyl)-1-azabicyclo[2.2.2]oct-3-yl)-3,5-difluorobenzamide
MX357676B (es)	2010-05-17	2018-07-18	Forum Pharmaceuticals Inc	Una forma cristalina de clorhidrato de (r)-7-cloro-n-(quinuclidin- 3-il)benzo[b]tiofeno-2-carboxamida monohidratado.
US8513430B2 (en)	2010-07-27	2013-08-20	High Point Pharmaceuticals, Llc	Substituted thiazol-2-ylamine derivatives, pharmaceutical compositions, and methods of use as 11-beta HSD1 modulators
EP3666272A1 (en)	2012-05-08	2020-06-17	Forum Pharmaceuticals Inc.	Use of encenicline in the treatment of cognitive impairment, alzheimer's disease, memory deficit
WO2014078568A1 (en)	2012-11-14	2014-05-22	The Johns Hopkins University	Methods and compositions for treating schizophrenia
US12448374B2 (en)	2018-06-07	2025-10-21	Disarm Therapeutics, Inc.	Inhibitors of SARM1
CN113164508B (zh)	2018-12-19	2025-07-08	达萨玛治疗公司	与神经保护剂组合的sarm1抑制剂
KR102629135B1 (ko)	2021-08-19	2024-01-29	단국대학교 천안캠퍼스 산학협력단	Kds2010을 유효성분으로 포함하는 주의력결핍 과잉행동장애의 예방 또는 치료용 약학적 조성물
KR102597711B1 (ko)	2021-08-20	2023-11-06	단국대학교 천안캠퍼스 산학협력단	Snap5114을 유효성분으로 포함하는 주의력결핍 과잉행동장애의 예방 또는 치료용 약학적 조성물
US20240350471A1 (en)	2021-08-20	2024-10-24	Dankook University Cheonan Campus Industry Academic Cooperation Foundation	Pharmaceutical composition for preventing or treating attention deficit/hyperactivity disorder
KR102684933B1 (ko)	2021-08-20	2024-07-16	단국대학교 천안캠퍼스 산학협력단	주의력결핍 과잉행동장애의 진단을 위한 gat-3의 용도

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US20020016334A1 (en) *	2000-07-31	2002-02-07	Coe Jotham Wadsworth	Pharmaceutical composition for the treatment of attention deficit hyperactivity disorder (ADHD)
US20030236287A1 (en) *	2002-05-03	2003-12-25	Piotrowski David W.	Positive allosteric modulators of the nicotinic acetylcholine receptor

2003
- 2003-11-28 CN CNA2003801084894A patent/CN1735441A/zh active Pending
- 2003-11-28 EA EA200500783A patent/EA200500783A1/ru unknown
- 2003-11-28 OA OA1200500174A patent/OA12969A/en unknown
- 2003-11-28 AU AU2003283656A patent/AU2003283656A1/en not_active Abandoned
- 2003-11-28 AP AP2005003336A patent/AP2005003336A0/xx unknown
- 2003-11-28 MX MXPA05006336A patent/MXPA05006336A/es not_active Application Discontinuation
- 2003-11-28 PL PL377552A patent/PL377552A1/pl not_active Application Discontinuation
- 2003-11-28 JP JP2004558921A patent/JP2006510663A/ja active Pending
- 2003-11-28 HR HR20050522A patent/HRP20050522A2/hr not_active Application Discontinuation
- 2003-11-28 BR BR0317229-5A patent/BR0317229A/pt not_active IP Right Cessation
- 2003-11-28 WO PCT/IB2003/005542 patent/WO2004052461A1/en not_active Ceased
- 2003-11-28 KR KR1020057010591A patent/KR20050085538A/ko not_active Ceased
- 2003-11-28 CA CA002509142A patent/CA2509142A1/en not_active Abandoned
- 2003-11-28 EP EP03775637A patent/EP1572300A1/en not_active Withdrawn
2004
- 2004-10-12 US US10/963,922 patent/US20050107425A1/en not_active Abandoned
2005
- 2005-05-23 IS IS7858A patent/IS7858A/is unknown
- 2005-05-27 ZA ZA200504338A patent/ZA200504338B/en unknown
- 2005-06-10 CR CR7868A patent/CR7868A/es not_active Application Discontinuation
- 2005-06-10 EC EC2005005852A patent/ECSP055852A/es unknown
- 2005-06-10 MA MA28325A patent/MA27606A1/fr unknown
- 2005-06-10 TN TNP2005000158A patent/TNSN05158A1/fr unknown
- 2005-06-10 CO CO05056569A patent/CO5700801A2/es not_active Application Discontinuation
- 2005-06-29 NO NO20053185A patent/NO20053185L/no unknown

Also Published As

Publication number	Publication date
ZA200504338B (en)	2006-07-26
PL377552A1 (pl)	2006-02-06
AP2005003336A0 (en)	2005-06-30
IS7858A (is)	2005-05-23
CA2509142A1 (en)	2004-06-24
MA27606A1 (fr)	2005-11-01
CN1735441A (zh)	2006-02-15
HRP20050522A2 (en)	2005-12-31
EA200500783A1 (ru)	2005-12-29
NO20053185L (no)	2005-08-17
AU2003283656A1 (en)	2004-06-30
TNSN05158A1 (fr)	2007-05-14
KR20050085538A (ko)	2005-08-29
CR7868A (es)	2005-07-08
WO2004052461A1 (en)	2004-06-24
JP2006510663A (ja)	2006-03-30
MXPA05006336A (es)	2005-08-26
CO5700801A2 (es)	2006-11-30
BR0317229A (pt)	2005-11-01
US20050107425A1 (en)	2005-05-19
NO20053185D0 (no)	2005-06-29
ECSP055852A (es)	2005-09-20
EP1572300A1 (en)	2005-09-14

Publication	Publication Date	Title
AU2003279492A1 (en)	2004-06-30	Treatment of diseases with combinations of alpha 7 nicotinic acetylcholine receptor agonists and other compounds
AU2004206107A1 (en)	2004-08-05	Treatment of diseases with alpha-7 nach receptor full agonists
EP1432707B1 (en)	2012-03-28	Azabicyclic-substituted fused-heteroaryl compounds for the treatment of disease
US20050107425A1 (en)	2005-05-19	Treatment of attention defecit hyperactivity disorder
WO2003070732A1 (en)	2003-08-28	Fused bicyclic-n-bridged-heteroaromatic carboxamides for the treatment of disease
CA2460075A1 (en)	2003-03-20	Substituted 7-aza[2.2.1] bicycloheptanes for the treatment of diseases
JP2006506395A (ja)	2006-02-23	ＣＮＳ疾患の治療のための、α７ニコチンアゴニスト活性及び５ＨＴ３アンタゴニスト活性を有する化合物
WO2004039366A1 (en)	2004-05-13	Nicotinic acetylcholine agonists in the treatment of glaucoma and retinal neuropathy
CN103443075A (zh)	2013-12-11	作为烟碱型乙酰胆碱受体调节剂的吡咯衍生物在治疗神经变性障碍，例如阿耳茨海默氏病和帕金森氏病中的用途
AU2002339957A1 (en)	2003-04-14	Azabicyclic-substituted fused-heteroaryl compounds for the treatment of disease